This invention relates to herbicidally active sulfonylurea compounds, agriculturally suitable compositions containing them and their method of use as herbicides or plant growth regulants.
In the most common situation, the control of undesired vegetation is desired to permit the growth of useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such useful crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which the complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
Euporean Patent Application (EP-A) No. 83,975, published July 20, 1983, discloses herbicidal benzenesulfonamides of formula ##STR1## wherein Q is selected from various five or six-membered aromatic or partially unsaturated heterocyclic rings containing 2 or 3 heteroatoms selected from O, S or NR.
U.S. Pat. No. 4,368,069 discloses herbicidal benzenesulfonamides of formula ##STR2## wherein R is --(CR.sub.5 R.sub.6).sub.n --R.sub.2 ;
n is 0 or 1; and PA1 R.sub.2 may be C.sub.2 -C.sub.5 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl or C.sub.2 -C.sub.3 alkenyl substituted with 1-3 chlorine atoms. PA1 Q.sup.1 is a 6-membered aromatic heterocycle containing one to three N atoms. PA1 B and C are independently H, halogen, NO.sub.2, C.sub.1 -C.sub.8 alkyl, CO.sub.2 R, etc.; and PA1 D is H or C.sub.1 -C.sub.8 alkyl. PA1 Q is an unsubstituted or substituted five-membered heterocyclic radical which is bound by way of a carbon atom and which contains 2 or 3 identical or different heteroatoms. PA1 R.sub.2 is H, Cl, Br, F, CF.sub.3 or OCH.sub.3 ; PA1 R.sub.9 is H or C.sub.1 -C.sub.3 alkyl; etc. PA1 R is H or CH.sub.3 ; PA1 L is ##STR9## n is 0 or 1; R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, CN, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CO.sub.2 R.sup.III, CH.sub.2 CN, CH.sub.2 OCH.sub.3 or CH.sub.2 SCH.sub.3 ; PA1 R.sup.I is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy; PA1 R.sup.II is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sup.I and R.sup.II may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sup.III is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 R.sub.2 is C.sub.1 -C.sub.3 alkyl; PA1 Q is a 3- or 4-membered heterocyclic ring which contains one heteroatom selected from O, S and NR.sub.3, or a 3- or 4-membered carbocyclic ring in which one carbon atom may optionally be in the form of a carbonyl group, or a fully-saturated 5- or 6-membered carbocyclic ring, and Q may be optionally substituted with 1-4 substituents selected from halogen, CN, OH, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.2 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, (C.sub.1 -C.sub.4 alkyl)aminosulfamyl and di(C.sub.1 -C.sub.4 alkyl)aminosulfamoyl; PA1 R.sub.3 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.12 is H or OR.sub.14 ; PA1 R.sub.13 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.14 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.4 haloalkynyl, C.sub.2 -C.sub.4 alkylcarbonyl, C(O)NR.sub.15 R.sub.16, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 alkoxyalkyl or C.sub.2 -C.sub.4 alkylthioalkyl; PA1 R.sub.15 and R.sub.16 are independently H or C.sub.1 -C.sub.2 alkyl; PA1 A is ##STR10## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, ##STR11## or or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.6 is H or CH.sub.3 ; PA1 Z is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 Y.sub.2 is H or CH.sub.3 ; PA1 X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA1 Y.sub.3 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; and PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or CH.sub.2 OCH.sub.3 ; PA1 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (b) when X or Y is OCF.sub.2 H, then Z is CH; PA1 (c) when L is L-2 or L-3, then the Q substituent and the sulfonylurea bridge are on adjacent carbon atoms; PA1 (d) when W is S, then R is H, A is A-1, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3 or CH(OCH.sub.3).sub.2 ; PA1 (e) the total number of carbon atoms of R.sub.12 and R.sub.13 must be less than or equal to four; and PA1 (f) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of R.sub.1 must be less than or equal to two and the number of carbons of Q must be less than or equal to six. PA1 R.sub.7 is H, F, Cl, Br, CN, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.8 is H, F, Cl, Br, I, CN, OH, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.2 -C.sub.3 alkoxycarbonyl, di(C.sub.1 -C.sub.3 alkyl)aminosulfamoyl, C.sub.1 -C.sub.3 alkylthio or C.sub.1 -C.sub.3 alkylsulfonyl; PA1 R.sub.9 and R.sub.10 are independently H, CH.sub.3, F, Cl or may be taken together to form C.dbd.O; and PA1 R.sub.11 is H or C.sub.1 -C.sub.3 alkyl; PA1 (a) when R.sub.7 and R.sub.8 are attached to the same carbon atoms as in Q-1, Q-2 or Q-3, or in Q-4 through Q-10, and R.sub.7 is OCH.sub.3, then R.sub.8 is other than F, Cl, Br, I or OH; and PA1 (b) when R.sub.7 and R.sub.8 are attached to the same carbon atom as in Q-1, Q-2 or Q-3, or in Q-4 through Q-10, and R.sub.8 is F, Cl, Br, I or OH, then R.sub.7 is other than OCH.sub.3. PA1 A is A-1, PA1 W is O; and PA1 R is H. PA1 R.sub.1 is selected from H, F, Cl, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CH.sub.2 OCH.sub.3 or CH.sub.2 SCH.sub.3 ; PA1 R.sub.13 is H or CH.sub.3 ; PA1 R.sub.14 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C.tbd.CH; PA1 X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2, CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, CH.sub.2 OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3. PA1 L is L-1; and PA1 Q is Q-1, Q-2 or Q-4. PA1 R.sub.1 is H, Cl, CH.sub.3, OCH.sub.3 or SCH.sub.3 and is not in the 4-position; PA1 R.sub.7 is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.8 is H, F, Cl, CH.sub.3 or OCH.sub.3 ; and PA1 R.sub.9 and R.sub.10 are independently H, CH.sub.3, F or Cl. PA1 L is L-2 or L-3; and PA1 Q is Q-1, Q-2 or Q-4. PA1 R.sub.1 is H; PA1 R.sub.7 is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.8 is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.9 and R.sub.10 are independently H, CH.sub.3, F or Cl; and PA1 R.sub.11 is H or CH.sub.3. PA1 L is L-4 or L-5; and PA1 Q is Q-1, Q-2 or Q-4. PA1 R.sub.1 is H; PA1 R.sub.7 is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.8 is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.9 and R.sub.10 are independently H, CH.sub.3, F or Cl; and PA1 R.sub.11 is H or CH.sub.3. PA1 L is L-6; and PA1 Q is Q-1, Q-2 or Q-4. PA1 R.sub.1 is H; PA1 R.sub.7 is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.8 is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.9 and R.sub.10 are independently H, CH.sub.3, F or Cl; and PA1 R.sub.11 is H or CH.sub.3. PA1 "The Chemistry of Heterocyclic Compounds", a series published by Interscience Publishers, Inc., New York and London; PA1 "Pyrimidines", Vol. 16 of the same series by D. J. Brown; PA1 "s-Triazines and Derivatives", Vol. 13 of the same series by E. M. Smolin and L. Rapaport; and PA1 F. C. Schaefer, U.S. Pat. No. 3,154,547 and K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812 (1963), which describe the synthesis of triazines.
European Patent Application (EP-A) No. 85,476, published Aug. 10, 1983, discloses herbicidal benzenesulfonamides of formulae ##STR3## wherein Q is selected from various 5-membered aromatic heterocycles, and their dihydro and tetrahydro analogs, which contain one heteroatom selected from O, S or NR, or Q is a saturated or partially unsaturated 6-membered ring containing one heteroatom selected from O or S; and
South African Patent Application 83/8416, published May, 1984, discloses herbicidal benzenesulfonamides of formula ##STR4## wherein A is an unsaturated or only partially saturated 5- or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms.
Herbicidal thiophene sulfonamides are disclosed in European Patent Application (EP-A) Nos. 30,142, published June 10, 1981, and 97,122, published Dec. 28, 1983, and in U.S. Pat. Nos. 4,127,405, 4,169,719, 4,398,939 and 4,441,910.
No. EP-A-95,925, published Dec. 7, 1983, discloses herbicidal pyrazolesulfonamides in which the group adjacent to the sulfonamide moiety may be selected from H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, OR.sub.16, CO.sub.2 R.sub.23, S(O).sub.n R.sub.24 or SO.sub.2 NR.sub.19 R.sub.20.
No. EP-A-87,780, published Sept. 7, 1983 discloses pyrazole sulfonamides of general formula ##STR5## wherein A is H, C.sub.1 -C.sub.8 alkyl or optionally substituted phenyl;
No. EP-A-96,003, published Nov. 28, 1983, discloses herbicidal compounds of general formul ##STR6## wherein R.sub.1 is H or C.sub.1 -C.sub.3 alkyl; and
Herbicidal pyridinesulfonamides are disclosed in European Patent Application (EP-A) Nos. 13,480 published July 23, 1980, 35,893 published Sept. 16, 1981, 97,122 published Dec. 28, 1983 and 103,543 published Mar. 21, 1984 and in U.S. Pat. No. 4,435,206.
U.S. Pat. No. 4,420,325 discloses herbicidal sulfonamides of the following formula ##STR7## wherein R.sub.1 is F, Cl, Br, CF.sub.3, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkyl, NO.sub.2, CO.sub.2 R.sub.4, SO.sub.2 R.sub.5, SO.sub.2 NR.sub.6 R.sub.7, SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 OCH.sub.2 CF.sub.3, OSO.sub.2 R.sub.5 or CH.sub.2 L;